5 & 7 John St: An Extraordinary Dual-Parcel Estate Redefining Elite Living in Greenwich

Date of Publishing: December 11, 2025

Few properties in Greenwich Real Estate offer the rare combination of architectural pedigree, legacy-scale acreage, and resort-style amenities found at 5 & 7 John St. Listed at $24,000,000, this extraordinary compound spans nearly 15 acres atop one of the highest elevations in the region, providing sweeping views of the surrounding backcountry. Originally completed in 1937 by renowned architect Augusta L. Noel, best known for designing the Whitney Museum, the estate blends Old World craftsmanship with contemporary luxury after a full restoration and expansion completed in 1989.

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Heritage Architecture Meets Resort-Level Amenities

Across 15,820 square feet, the main residence at 5 & 7 John St features 10 bedrooms and 16 bathrooms, complemented by grand formal rooms, eleven fireplaces, an elevator, a sauna, and an expansive chef’s kitchen. The interior design showcases Noel’s signature stonework, slate roofing, and meticulous attention to symmetry, while recent enhancements elevate the residence for modern living.

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According to listing agent Shelly Tretter Lynch, the home has been carefully preserved by owners who recognized the architectural significance of the property. “The current stewards have invested tremendous effort into maintaining both its historic identity and its livability,” Lynch told Luxury Houses Magazine, emphasizing that every improvement was made with long-term preservation in mind.

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Outdoor amenities rival those of a private club, including indoor and outdoor pools, a full tennis house with an adjacent tennis court, multiple fountains, immaculate paddocks, and a beautifully restored stable complex. The estate also includes two guest cottages, a carriage house, and a series of interconnected garden rooms designed by acclaimed landscape architect Jacqueline Osty, celebrated for her work on Paris’s grand parks and boulevards.

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SEE MORE: Connecticut Luxury at Its Finest: A Remarkable One-of-a-Kind Masterpiece for $5.2 Million

A Coveted Backcountry Location With Rich Provenance

The backcountry of Greenwich has long been considered one of the most exclusive residential enclaves in Connecticut Real Estate, favored for its exceptional privacy, wooded landscapes, and proximity to New York City. Sitting near the summit of John Street, the estate enjoys a level, parklike setting rarely found in the region, with quick access to nearby equestrian trails, country clubs, fine dining, and boutique shopping.

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“John Street has always represented the pinnacle of backcountry living,” Lynch shared in a conversation with Luxury Houses, adding that the property’s dual-parcel configuration provides flexibility for generational families seeking both scale and seclusion. The agent further noted that opportunities of this magnitude “simply do not reappear in the market very often.”

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SEE MORE: Custom-Built Connecticut Estate Boasting Unparalleled Excellence and Forever Views for $4.5 Million

Transaction History and Long-Term Market Perspective

The property was brought to market on December 9, 2025, at its current price of $24 million, following a previous listing at $28.5 million in both 2024 and early 2025. Its price evolution reflects broader market dynamics affecting legacy estates and ultra-luxury transactions across Fairfield County.

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Lynch explained that demand for landmark estates has strengthened as buyers increasingly value acreage, privacy, and architectural significance. “We’ve seen a resurgence of interest in properties with provenance—homes that tell a story,” she said, noting that the estate at 5 & 7 John St satisfies a rare combination of history and livability that high-net-worth clients seek post-2020.

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SEE MORE: Connecticut Modern Estate by Renowned Architect William D. Earls Seeks $15.945 Million

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Lifestyle and Community: The Best of Greenwich Backcountry

Residents of John Street enjoy a lifestyle defined by tranquility, green space, and convenient access to the cultural attractions of downtown Greenwich. Top-rated schools, gourmet markets, and refined dining are just minutes away, while the Merritt Parkway and Metro-North Railroad ensure effortless commuting to Manhattan. The backcountry community is known for its equestrian culture, nature preserves, and spacious properties, making it a premier destination for luxury buyers seeking privacy without sacrificing convenience.

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This estate’s extensive amenities—pools, stables, guest houses, and entertainment structures—create what Lynch describes as “a self-contained world.” In her words to Luxury Houses Magazine, “It’s a property meant to be experienced, a sanctuary where every detail has been curated for elegance, comfort, and generational enjoyment.”

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For complete details, readers can explore the full property information for 5 & 7 John St on Zillow and visit the listing agent’s page at Compass Connecticut, LLC, represented by Shelly Tretter Lynch.

* This property might not for sale at the moment you read this post; please check property status at the above Zillow or Agent website links*